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Organocatalytic Tandem Synthesis of Chiral Hexacyclic Bisindoles from Propargylic 3-Methyleneindoles with 2-Indolylmethanols.

Kanghua RuiHaorui GuAlemayehu Gashaw WoldegiorgisXu-Feng Lin
Published in: Organic letters (2023)
A novel chiral phosphoric acid-catalyzed tandem regioselective 1,6-addition/double intramolecular nucleophilic addition annulation of the propargylic 3-methyleneindoles in situ generated from α-indolyl propargylic alcohols with 2-indolylmethanols has been developed. The methodology afforded the new chiral trifluoromethyl pentalenobisindoles bearing an all-carbon quaternary stereogenic center in generally good yields with excellent enantioselectivities.
Keyphrases
  • capillary electrophoresis
  • ionic liquid
  • room temperature
  • mass spectrometry
  • energy transfer